Cartoon illustrations for a marketing campaign

We are an IT managed services provider - meaning we basically provide a full service IT department and computer support help desk for small businesses who do not have their own IT staff. I have a concept for a postcard marketing campaign featuring several cartoons. For the first one I have in mind a postcard that speaks to small business owners that are wearing a lot of hats and trying to do what they do best plus everything else. Sort of the chief cook and bottle washer idiom. One idea is to have a "small business owner" guy who is split into 4 quarters - each quarter with the distinctive dress of a various role he plays. One would be a professional (jacket, tie, briefcase), one would be a computer guy (one hand typing on a computer, pocket protector, etc.), one would be a janitor (mop and bucket), and I don't know what the other would be - some other job role identifiable by just a leg... The second one is pretty basic - a frustrated computer user. The third postcard will address security concerns. I don't really have a good concept for what that cartoon looks like, but the basic idea is the small business owner concerned about keeping out the bad guys - hackers, viruses, malware, etc. The fourth postcard will address backup and disaster recovery. That's everything from accidentally deleting a file from the server to a major disaster like fire or tornado. The cartoon wouldn't need to address that wide a range, but somehow communicate a small business owner worrying about important data being lost. So the project is to create the four cartoons that have some continuity - if nothing else, in illustration/cartooning style. The first one, I'm pretty set on the concept (the small business owner divided in 4 quadrants), but the rest of them have some latitude and creative freedom.